The Trials and Hardships of a Sarcastic Gay Teenage Emissary
by rose-amour
Summary: Okay, maybe Stiles isn't gay. But he's definitely something. If one thing's for sure, Stiles is definitely lonely. He's tired of being the only virgin in their group of friends, though surpassing all of them in the way of intellect and maturity (most of the time). Stiles needs to get Stiles laid. (Or, the obligatory Sterek porn piece with a generous helping of smut and bad humor.)


**A/N: **This was originally posted in chapter format on Archive Of Our Own. It's the first fic that I've ever written, and after getting as much traffic as it did, I decided to turn it into a series (so there will be more of this story in due time). Be honest, and leave reviews and whathaveyou so I know what I'm doing right and what I should improve on. Thank you for taking the time to read my work; I really hope you enjoy it!

* * *

Okay, maybe Stiles isn't gay. But he's definitely something.

Stiles once tried to come out to his father, but he didn't believe him. He blew it off as a joke, saying, "Stiles, you're _not_ gay." He's dropped hints to his friends, especially to Scott, but it's like no one has been paying attention to him. Maybe they thought he was just acting desperate, because he really does hit on anything with a pulse. Stiles isn't necessarily strictly gay. He's just Stiles.

If one thing's for sure, Stiles is definitely lonely. He's tired of being the only virgin in their group of friends, though surpassing all of them in the way of intellect and maturity (most of the time). It's like Stiles has learned so much since the supernatural world enveloped his life, but Scott has remained constant in his oblivious 15 year-old mindset. Stiles feels older than most of the group, though that definitely isn't wholly true. Maybe he just has a distorted superiority complex, which is ironic, because of how much he loathes himself.

Stiles has looked for love everywhere. He's tried online dating, he's tried clubs outside of Beacon Hills, hell, he's looked to the mountains and the rooftops too.

Maybe it's not time for Stiles to find love. After beating the Darach and the Alpha Pack, Deaton takes Stiles under his wing to teach him more about his "spark." He tells him that he could become a druid if it is what he desires, and said he would teach him how to harvest the power of the Nematon left behind by the Darach. Deaton says that, in itself, the tree is not evil. He has no fear in his heart that Stiles will use his power for evil, so he's very enthusiastic about teaching Stiles how to become a druid. Stiles has been working for him for a few months now alongside Scott at his veterinary practice, with Deaton often giving him new reading materials and meeting him at the Nematon after hours for lessons in control and strength. It's looking promising for Stiles; maybe now he will be of some use to the pack. He's more tired than anyone of showing up late to the attacks, being the one to find the bodies. It has become far too much for him to handle.

* * *

Stiles is at the loft with the whole pack for tonight's pack meeting. Although, as of late, pack meetings have become somewhat of a joke with there being no real threats or imminent danger. Pack meetings are more like catch-up days for everyone, updating each other on their lives and sharing new stories. But seriously, that's what Facebook is for.

Derek talks about what he always talks about. He discusses preparation and training for the next confrontation. It's weird now, because he shares his alpha status with Scott, sort of. Scott being a "true alpha" doesn't really give him any power over Derek's pack, so essentially, he's the alpha of his own pack, but he doesn't have a pack. Derek agreed to let him stay with their pack, and Scott may have a more prominent say now, but Derek gets the final word. It's a really messy situation, really.

Stiles likes to feel important to the pack, but he knows he really isn't. At least, not where he is in his druid training. Stiles has always been the one with the plan, but now, he's kind of a sitting duck, and he hates it. He watches the pack meeting ensue and listens to them all argue and babble. The egos in the room begin to suffocate him, so he goes to the bathroom.

When he comes back, each member of the pack is in their respective spots - Scott and Allison together on the couch, snuggling, Isaac on the floor in front of them, sitting back on Scott's legs, Peter leaning against the wall, Derek pulling DVD's out of the cupboard. Stiles takes a seat across the room on the floor, trying not to draw attention to himself, but he knows his pack mates will think something is wrong. Thankfully, no one says anything.

Derek kneeling in front of the TV stand is torture. His ass is in perfect view; Stiles really wants to just run up and smack it and run away giggling. But in all seriousness, he can't help but stare in envy at the dark-wash skinny jeans that get to showcase Derek's ass. He finds the DVD he's looking for and pops it in. He turns back around and stands up, his shirt ruffled up, exposing the bottom of his midriff. Derek's V is glorious. Stiles averts his eyes quickly, so as to not catch Derek's gaze. He'd never want him to know about his schoolboy crush on him. Derek says, "Okay, so there's three votes for _the Avengers_, and one vote for _Pitch Perfect_. Sorry, Isaac. Maybe next week."

Just then, as they're all about to start the movie, Cora blunders into the loft, making herself known as usual. In her own element, she can be loud, sarcastic, and witty, which is a great match for Derek's character. Derek huffs, rolling his eyes, and asks, "Where the hell have you been? You're an hour and a half late."

"Oh, come on. Don't get your panties in a bunch, Derek. That is, if you're even wearing any." This gets a good laugh from the whole room, from everyone except for Derek.

He snarls, his eyes glowing red. "This isn't funny, Cora. Pack meetings are important business."

"Why? What is the threat his week - the dwindling deer population, or your utter lack of a social life?" The room is quite literally howling with laughter. Stiles chuckles quietly to himself. Derek has no response for her, just growling and flashing red eyes. She continues, "Will you just get laid already?"

"Shut. Up."

"No, seriously. New mission, guys: we need to get Derek laid."

Peter inserts himself into the banter. "I have a brilliant idea. Let's get him a puppy." Okay, that one makes Stiles laugh.

Cora gets herself a cold beverage from the fridge and goes to sit next to Stiles. This is really weird, considering the fact that she really cannot stand him, and she's made that abundantly clear on many occasions.

Derek yells, silencing everyone, "I DON'T NEED ANYBODY'S HELP!"

Stiles needs to get Stiles laid. Stiles needs to get Stiles laid very soon, many times. Many times in a row, in many different places. Hell - even with many different people, in many different situations. He doesn't care if these thoughts make him feel like a whore.

Derek continues, "...so you can all just _shut the fuck up._" And they do. And they watch the movie, and halfway through, Stiles gets a text from _Sourwolf._ It reads: "can you hang back a bit after the meeting?" He realizes his heart leaps at the sight of Derek's contact popping up on his screen, but everyone's so into the movie that he doesn't think anyone hears.

He fumbles a reply. "You got it, hoss." He can see Derek's lap light up, but his face is unchanging.

Derek sends another text, this one saying, "Sorry, didn't want to draw attention by asking you in front of everyone. Didn't want anyone to think I was favoring you. ;)"

_HOLY FUCKING SHIT OHMYGOD DEREK FUCKING HALE SENT ME A FUCKING WINKY FACE I THINK I'M MELTING ON THE INSIDE SMOLDERING IN THE HEAT OF A THOUSAND DYING SUNS THAT ARE THE ESSENCE OF DEREK HALE AND OHMYGOD - _"It's cool."

* * *

After the movie ends, everyone starts to pack up and leave. Cora and Peter decide to go to the diner, leaving Derek behind. To make it seem less strange that he's hanging back, he tells Scott he's going to the bathroom.

Stiles' heart leaps when he walks back down the hallway from the bathroom and everyone has left. He hasn't been a lone with Derek much, but he never saw the two as friends, really. He saw Derek as a sort of god, actually, with a perfect body and a broken heart. It's really sexy to Stiles. But Stiles doesn't expect anything to happen - never in his wildest dreams could he see himself with Derek freaking Hale. He's leaning against his kitchen counter, drinking a cup of coffee. The man never sleeps, he's sure. "Sorry if I freaked you out asking you to hang out. It's nothing big, I swear."

"Am I in trouble?" He raises an eyebrow, a shot at being flirtatious, but Derek shakes his head.

"Coffee?"

Stiles shakes his head. "No, I actually want to get some _sleep_ tonight."

"Anyway, I was going to suggest that maybe we should spend more time together, I don't know - _bonding _- because of your training and your new position as our emissary." Stiles can feel his heart sink into his stomach. _Fuck yes. _"I'd like to be involved, if you'd allow that. Or at least, keep me updated on new developments."

Stiles will take any time he can with Derek. His crush is deeply-rooted. So much that Stiles dreams of having him in bed with him, lying there still, enjoying the sounds of his breath and the feel of skin against skin. _Oh god, what the hell is wrong with me? _"Sure, sounds good. I don't - I don't know what you were thinking, but we could get some curly fries or something."

Derek laughs. _Damn that grin of his. _"Sounds good. I'll text you."

Stiles leaves without another word, nodding and gathering his things, slinking out the door. He fears what he might have said had he given himself the chance to talk. Actually, he might have just jumped him right there on the spot.

The drive home from Derek's loft is challenging; Stiles finds it hard to drive in his Jeep with a hard-on.

Nevertheless, he gets home in one piece. His dad's not home, so Stiles frolics into the house, loving the freedom of not having to explain his whereabouts to his father. He stuffs his face with the only real food in his fridge - lunch meat and cheese - and heads upstairs for bed. He grabs some clothes to change into for bed, but as he pulls open his closet door, he hears his window fly open. It's Derek, standing there in all his glory, in Stiles' bedroom.

"Dude, I know I said we could spend more time together, but I didn't mean -"

"I just - I can't get something out of my head. But it's probably nothing. I'm sorry, I'll talk to you tomorrow -"

Stiles crosses the room and grabs his wrist before he can jump out the window again. "Derek, use your words."

He growls. "Your scent. It was...different tonight."

"You notice my scent?" Stiles chuckles, like he's _honored._

"Always." You can actually see the tension in Derek's frown lines. He's blushing. "And your heart started pounding both when you got my text and when you saw everyone had left."

"Probably too much Adderall today, man, I don't know. I took my second dose later than usual. Makes my heartbeat funky." Derek takes a few steps closer, getting into Stiles' personal space. His face is hard and unyielding, full of both anger and concern. He backs Stiles into the wall next to the window and starts sniffing the place on his neck between his jaw and his shoulder. "Whoa dude, personal space..."

"Do I scare you?" Derek leans back, a questioning look gracing his face. It's not something Stiles sees very often. Derek just isn't very expressive.

Stiles laughs, mostly out of discomfort. "Are you asking if I'm scared of the Big Bad Wolf? Because, to be honest, Derek, that's pretty cliché."

Derek grits his teeth and his eyes flash red, but his claws stay retracted as he reaches up a hand to grip Stiles' jaw so that he has no choice but to look him in the eye. "Answer the question."

"Listen to my heartbeat. No, Derek Hale,_ I am not scared of you._"

He lets Stiles go and steps back, shaking his head, confused. Stiles exhales deeply and sinks against the wall to a sitting position on the floor.

"Then what's going on? Aside from your usual hyperactive and snarky attitude, you were acting especially strange earlier. The most concerning part being you not saying a single word at the pack meeting."

He didn't even realize he hadn't spoken that evening, which, truthfully, was a rarity. "I...I'm not sure."

"You're lying." Derek grabs him by his jacket and pulls him back up, holding him against the wall, again, forcing him to meet his eyes. "I can tell."

"I... I'm not -" Stiles' heartbeat was pounding loudly in his ears, the only tangible sound being the rushing of blood to his head. His eyes well up.

"Stiles?"

Stiles inhales and exhales deeply, mocking meditative breathing. He rubs his eyes and laughs. "_Jesus_, Derek." He mumbles, and begins to regain his courage. Thank god his dad isn't home. "And here I thought nothing got past those keen werewolf senses."

Derek's eyes grow wide and he shakes his head again, confused. "I don't understand." He lets go of Stiles' jacket but still stands tall, right in his personal space.

"Please don't kill me for this..." He takes Derek's face in both hands and pulls him in, kissing him deeply and passionately. A tear streams down his face and for a moment, Derek doesn't react. But in seconds, Derek closes the gap between the two warm bodies, pressing Stiles against the wall, with one forearm leaning against the wall next to Stiles' head, and the other hand taking the back of Stiles' neck, deepening the kiss.

Derek finally pulls back and pants, "_Fuck,_ Stiles." He looks down for a second, taking his hand away from the back of Stiles' neck. He closes his eyes tight and shakes his head, dropping his gaze to the floor. He looks angry, disappointed, even. "You can't do something like that and expect me to be able to walk away."

"Then don't."

* * *

"Stiles, I can't do this." He runs a hand through his perfect blown-out black hair. Oh, how Stiles longs to run his fingers through that hair.

"Why not?" He grumbles out, jokingly upset, but truthfully in pain on the inside.

He huffs again, adding a growl this time for good measure, blurting out, "What do you _want_ from me?!"

"You really are a bumbling idiot, aren't you?" He pulls Derek back in, smirking, kissing him again.

He bites on Derek's bottom lip, and again, Derek pulls back to interject."Stiles, I don't... I don't want you to get hurt." Stiles rolls his eyes and shakes his head, but before he can protest, Derek continues, "I don't just want a one night stand. I can't do that."

"I can't believe I'm the one saying this, but Derek, for once, please just shut up and enjoy the moment." Stiles puts both arms around Derek's neck and flashes him a smile.

Derek grins wildly, releasing all inhibitions. "Okay, but you asked for it." He pins Stiles hard against the wall, gripping Stiles' hips with both hands, then slowly moves both hands up his shirt. Derek is a fantastic kisser, so incredibly passionate and strong. It seems as if he's really experienced, though Stiles has never actually seen him or heard of him being with anyone before. Except for, you know, Kate Argent. Sore subject. Derek pulls back shaking his head, gasping, "Wait, Stiles, aren't you a virgin?"

"Yes, and I'm _really_ trying to change that."

"Is that what this is to you?"

"No, Derek, I didn't mean it that way. Hey -" he grabs his face in both hands, his grip loosening into something soft and sincere. "Stop that. Actually, it's really your fault." Derek looks confused. "You in those devilish jeans..." His voice trails off as Derek laughs and swiftly lifts him up, moving him over onto the bed. This is what he wants, what he's wanted for so very long. He longs to touch - or lick, whichever he can get away with - every inch of Derek's perfectly chiseled body.

Derek may not have had a mad schoolboy crush on Stiles, but the thought of him always lingered in the back of his mind. He didn't think of Stiles often, but he's dreamt of him. He's dreamt of Stiles' fingers, specifically, and about trailing kisses one every cute little mole on his body. He finds his honesty and his sarcasm a beautiful match for his personality. Derek knows that under his overbearing demeanor, Stiles has a soft and gushy inside, and a broken heart like his. So when Stiles pounces on him, he may second guess himself, but realizes that this is indeed what he wants.

"Sit on the side of the bed." Stiles follows Derek's command. Derek gets on his knees in front of him, slowly pulling at Stiles' jacket and shirt to take them off. When he does, Stiles wants to feel even, so he (more violently than Derek) pulls off Derek's shirt. Though Stiles is no match for Derek's physique, there is a certain beauty in his soft complexion and barely visible muscle tone. He has some definition, but the lines aren't prominent or bold like Derek's. But Derek finds this incredibly appetizing, and trails bites and kisses from Stiles' neck, down his chest, right around his navel, and chews at the waistband of Stiles' pants. He looks up at Stiles, grinning madly. _Jesus fuck, this isn't happening._ "Off." Derek motions to Stiles' pants. "Everything."

"Okay, geez." He stands up in front of Derek and wiggles his pants and boxers off, discarding them across the room, and sits back on the edge of the bed. Derek rests one palm on each of Stiles' knees, and takes in the sight before him, accepting a very wonderful and disturbing new realization: Stiles has a _huge _dick. _Challenge accepted._

* * *

Stiles watches as Derek takes hold of the base of his erection, holding it steady so that he can drag his tongue from the base to the head, licking the skin around the slit. He slowly takes just the head into his mouth, swirling his tongue around as he does so, and Stiles whimpers. _This is torturous. _Stiles runs the fingers of his right hand through Derek's hair, enjoying being able to carry out one of many of his fantasies. Derek takes that as a sign to start slowly taking Stiles' length into his mouth, sucking lightly, using his tongue to put pressure on the underneath of Stiles' erection as he works it with both his hand and his mouth. And, _oh god,_ Derek looks up at Stiles, eyes flashing red, when a low growl reverberates through Derek's throat. "D...Derek..." Stiles tugs at Derek's hair, warning him, but Derek doesn't let go. Instead, he takes Sties' whole length into his mouth, allowing the head to bump against the back of his throat. "Fucking _hell,_ man." _It's like he's done this before. _Before long, Stiles comes, moaning Derek's name, while Derek greedily sucks down every last drop, wanting more.

As Stiles comes down from his high, watching Derek's perfect body slither up to reposition the two on the bed, he can't help but pinch himself. Never in his wildest dreams - okay, maybe in his wildest dreams - would he even think he had a shot with Derek. It was such a silly infatuation to have. But as he looks up at Derek, who's leaning over top of him with wild, hungry eyes, he realizes that _yes, _this is happening, _yes, _Derek is on top of him, and _yes, _this was always possible. Stiles drags his fingertips along this skin on Derek's chest, his gentle touch turning into something more fiendish and starved, and he gropes every piece of Derek he can. He explores his body intently, wanting more - so much more.

Derek isn't expecting it when Stiles flips the two over and begins kissing Derek from his chest up to his shoulder, and from his shoulder up his neck until his lips rest against Derek's ear. The hot breath sends shivers down Derek's spine. Arching his back, he moans, much sexier than when Stiles does, he realizes. Stiles whispers, dragging his lips along Derek's ear, "I want you to fuck me, Derek. I want you to fuck me so hard."

Derek shoots both hands up to grip Stiles' hips and pulls them hard against his own, insisting the touch, growling out, "Oh, yeah? Is that what you want?"

Stiles trails one hand down to Derek's neglected package, rubbing down on the fabric of his jeans teasingly. He doesn't move where his lips rest on Derek's ear and continues, "I want you to make me scream your name. Derek, I want you to _ruin me._" At that, Stiles can't whisper any more far-from-sweet nothings in Derek's ear, because in an instant, Derek is flipping them back over.

"You won't be able to walk for a week." Derek's hands run up and down Stiles' sides, and chuckles quietly. Stiles is already half-hard again, and Derek sighs jokingly. "Oh, to have the stamina of a teenager again." Before Stiles can make a snarky comeback, Derek presses a finger to his lips, then substitutes out his finger for his own lips, pressing a wild and sloppy kiss to Stiles' lips. Derek moves quickly into a standing position next to the bed, unbuckling his own belt, leaving Stiles with his eyes still shut and his lips still pursed. "Do you have any..."

Before Derek can finish, Stiles answers him. "Side table, in the drawer."

Derek sits on the side of Stiles' bed, completely naked, rifling through the bedside table drawer. "You know, I wouldn't be modest if I was you either," he says, not turning around, holding up one XXL condom between his fingers.

"No...no condom." Derek turns back to look him in the eyes, but before he can question, Stiles continues, "and yeah, I'm sure."

Derek fumbles in the drawer for the lube before crawling back on the bed to straddle Stiles' legs. Stiles throws his head back and closes his eyes, feeling one cold, lubed-up finger teasing his rim. He whimpers out, "Jesus _Christ."_

"I prefer to be called Derek." Stiles wants to throw his a comeback about how cliché that comment was, but before he can, Derek is slowly working one finger into Stiles' ass. Surprisingly, Stiles adjusts to the pressure quickly, making Derek wonder if he's ever experimented with himself before, but that just makes him more turned on.

When the one finger is comfortable and it's completely in, torturing Stiles by brushing against his prostate, Stiles blurts out rather aggressively, "_Fuck..._fucking _more, _Derek. I can take it." And he can. He can take two fingers, then three, and by now he's practically suffocating from the lack of release. He grabs Derek's free wrist and writhes, "Just _fuck _me, Derek."

Stiles let's go of his grip on Derek's arm and it's not long until he feels the cold, foreign feeling of Derek's head against his hole. Derek slowly inserts his head into Stiles' ass without any further encouragement, using all of his will to not plow into Stiles like an animal. Stiles hisses from the pain and adjusts himself, gritting his teeth. "I'm... I'm good." Derek moves closer, parallel to Stiles' body, pushing more of his length in slowly as Stiles adjusts. The pain isn't unbearable, but it's really unpleasant, and Stiles has to grit his teeth so as to not let an embarrassing noise slip from his mouth. "Shhhit."

"Would it help if I said that it gets much better?"

"Definitely," Stiles says, twisting his default smirk into something much more sweet and soft.

Derek bottoms out, and Stiles can almost immediately feel a sense of euphoria wash over his entire being, inside and out. After he allows his insides to rearrange themselves, staring into Derek's eyes for an eternity, he grips Derek's biceps and nods, saying, "move." Derek slowly, agonizingly begins to move, pulling almost all the way out before pushing slowly back in. Stiles grips Derek's ass cheeks, and when Derek pulls back almost all the way again, Stiles' pulls Derek back in hard. His hands move from Derek's ass after a few more hard thrusts up to his back, the sensation of Derek's dick abusing his prostate causing him to dig his human nails into the skin of Derek's back. Derek quite literally howls with pleasure and moves to bite into Stiles' neck, leaving what will be a vibrant bruise. Stiles blurts out, "Oh my _fuck_" as he grows closer to orgasm. "Derek, I'm gonna -" And before Stiles can finish, Derek moves one hand from holding himself up to give attention to Stiles' erection. Stiles has never felt so stimulated in his life - never such a feeling of ecstasy and bliss such as this.

Derek growls, his eyes flashing red, and they both come simultaneously - quite an achievement. But who is he kidding, Derek did everything. He just sat there. Derek stays in his position for a moment, riding out his orgasm, then pulls out with an audible _plop. _He falls next to Stiles on the bed, panting. Between breaths, he mutters, "That...that was the b-best sex I've _ever_ had." Stiles' mouth hangs agape, and Derek nods, adding, "yup."

Stiles shifts, looming over Derek now. "I - I don't want this to be a one-night stand either."

Derek moves one hand to caress Stiles' face, admiring the sincerity in his expression and the meaning in his voice. "Then it won't."

* * *

Stiles stumbles down the stairs the following morning to find his father in the kitchen, pouring himself a cup of coffee. Stiles grabs a granola bar out of the cupboard, unintentionally exposing his bruised neck to his father.

His dad points and asks, "Do I even want to know?"

Stiles exhales dramatically and grabs his keys off the kitchen counter and replies, "Probably not."

"I'll see you after school, son."


End file.
